• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio

indanorex

wungchow

wungchow

Bluelighter
Joined
Dec 12, 2006
Messages
893
Location
nyc
16112-96-2.gif


indanorex is an old stimulant anorectic, not sure about the mechanism of action or its potency as compared to d-amphetamine.

however, I wonder if a structure-minimized methylenedioxy analog would behave in a manner similar to MDMA.. there's not much steric bulk surrounding the nitrogen
 

Attachments

  • mdindan.gif
    mdindan.gif
    2.1 KB · Views: 84
Dopamine reuptake. The distance between the aromatic group & the amine group will be just about the same as it is in things like cocaine & CFT (and some of the weirder fencamfamine derivatives outlined in a thesis paper I've got). Very much doubt it'll cause dopamine release as they require the phenethylamine skeleton as a rule
 
on a tryptamine i would think greater psychedelic potential would be realized by having the MD ring affix to the 4,5 positions, not the 5,6
 
^

true, though it appears it may be 'behave' more like a tryptamine than a PEA (seems to not quite conform to either)

but that is hard to say...i wonder if its anorectic effect (indanorex) has a notable serotonergic component as that may yield some insight
 
MDAI is a selective serotonin releaser,or do you have any info in regards to its SERT activity?
 
It is =/ ? Hmm, okay. Can you provide the references for that?
I don't know where I learnt(?) that MDAI was a selective SERT inhibitor unfortunately. So it acts both on the 5-HT VMAT and SERT? Or *just* VMAT? (I understand VMAT is the mechanism for releasers as opposed to reuptake inhibitors)
 
MDAI though indeeds looks very much like a PEA that loops back on itself and thus one would anticipate a high liklihood for MDMA like activity which indeed it has to a small degree as a potent serotonin releaser

though it does not sub for MDMA, but does for MBDB and is not noted to be neurotoxic
 
Isn't MDAI one of the other two drugs Nichols from substituted for MDMA to a degree?
 
^
MDAI and MBDB both sub to a degree i believe, but not enough to consider a true substitute

MDAI and MBDB sub for one another to a high degree
 
Ham-milton: Yeah in the paper "Non-neurotoxic tetralin and indan analogs of MDA" by Nichols compounds 3a&b produced the MDMA cue in MDMA trained rats.
3a = 5,6-methylenedioxy-2-aminoindan (also known as MDAI)
3b = 6,7-methylenedioxy-2-aminotetralin
 
MDAI has less dopaminergic activity than IAP, so if you found IAP disappointing, expect to be similarly disappointed by it, if not moreso by MDAI. Personally I really liked IAP, especially with a little amphetamine thrown in to give it that extra oomph (actually feels a lot like MDA, but without the evil comedown, with a pinch of amphetamine added)! :D

At least it will not have the evil comedown afterwards as it can't be metabolized to alphamethyldopamine like MDA/MDMA (that's the stuff responsible for the hideous depression a couple of days afterwards)
 
the second substance shown in the top post,
Is more closely related to the aminomethyl indans that nichols has shown to be active 5HT2a agonists with the equivalent to a 3,4,5 trimethoxy (mescaline) pattern on the phenyl and a 2,5 dimethoxy 4 bromo (2-CB)equivalent pattern. In fact the substance is the MDA version.
So it is highly likely to be a 5ht2a agonist and I ould go further to suggest that if the SAR works it will be more potent as an agonist than MDA. whether it has any effect on DAT SERT NERT VMAT is dependent on whether the transporter has any affinity for it and whether it can move it. from the distances it meets the requirements for DAT affinity.
The alpha methyl is likely to be redundant BTW.
MDAI has the amino group attached directly to the indan ring rather than a methyl spacer.
I love cut n paste pointless speculative pharmacology... :)
V
 
Besides the J. Med. Chem. (33, 703-710 , 1990) paper,theres one about "the monoamine releasing and uptake inhibition properties of MDMA and PCA analogs" (Eur. J. Pharmacol., 200 , 9-16 , 1991),mentioning MDA,MDMA,MBDB, MMA,PCA,PIA (...my darling!),MDAI,MMAI,IAI,6-CAT plus a few of their potential catechol metabolites like DHAI.Quite a detailed paper with a lengthy discussion.Things f&b et al tend to palaver about when going into toxicity issues on that cluster of compounds...

If you're interested you can PM me for a copy.
 
I'm thinking that the methyl spacer before the amino group will distinguish this compound from IAP significantly, and possibly allow the same reversal effect at SERT.
 
You must log in or register to reply here.
Top